


Practice Makes... Your Friendship a Little Complicated

by allfordean



Series: Fic Requests [3]
Category: Supernatural
Genre: Alternate Universe - High School, M/M
Language: English
Status: Completed
Published: 2015-04-23
Updated: 2015-04-23
Packaged: 2018-03-25 11:21:33
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,513
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3808468
Author URL: https://archiveofourown.org/users/allfordean/pseuds/allfordean
Summary: <blockquote class="userstuff">
              <p>Dean, being the great friend that he is, decides to take Castiel out on his first date. Of course, it's not a *real* date. It's just practice. ...Right?</p>
            </blockquote>





	Practice Makes... Your Friendship a Little Complicated

**Author's Note:**

> This was sort of a [prompt](http://essentialcas.tumblr.com/post/102413534889/destiel-high-school-college-au-where-dean-and-cas) that I got on Tumblr like half a year ago. I'm moving it here because of reasons.

“You’re kidding me.”

Castiel sighed and turned away from his friend, straining not to roll his eyes as he slammed his locker shut and began to walk down the hall. “I’m not kidding, Dean.”

The taller boy followed closely behind, eyes wide as he asked, “Seriously, you’ve never dated?”

“Never.” Frowning, Castiel stopped to face his friend once again. “Dean, you’ve been my closest friend for over six years. If I had ever gone on date, you would have known about it.” Under his breath, he mumbled, “I certainly know more than I’d like to about  _your_  love life.”

Blinking, Dean pursed his lips, glancing up before raising his brows and looking back at his friend. “But what about Meg?”

“What about her?” the blue-eyed boy asked, his voice flat as he tightened his grip on the straps of his backpack.

“She used to hit on you, like, a  _lot_ , before she switched schools.” Quirking a brow, Dean tilted his head pointedly. “You’re telling me nothing ever happened?”

"No,” Castiel said, turning back to the hallway and making his way toward their next class. “Nothing happened, and I’d appreciate it if you’d drop the subject.”

 

It was only a week later, when Dean was sitting on Castiel’s bed, that the issue came up again.

“I’m telling you, Cas,” the boy said, leaning back against his friend’s pillow, “Hannah totally likes you.”

Not bothering to look up from his desk, Castiel said, “Dean, you’re here to study with me, not encourage me to ask someone out.”

Dean shrugged. “Hey, I’m not saying you should ask her out. Hell, she might ask  _you_. I’m just sayin’… be ready for it, is all.”

Shaking his head, Cas lifted his head to lock eyes with his friend. “Why do you care so much about-“

“It’s not that I  _care_ , Cas, it’s that I… I kinda feel bad for you.”

"Damn it, Dean, I don’t need to be pitied.”

Dean sat up, crossing his arms as he said, “I don’t  _pity_  you, either, man, I just… Dude, in all your 17 years of life, you’ve never even  _kissed_  someone.”

“I have siblings who didn’t have their first kiss until they were in their twenties.”

“And you wanna be like them?”

Castiel clenched his fist to keep from biting his tongue. “I don’t care about finding a relationship right now.”

“Yeah, but you don’t know what you’re missing,” Dean said, eyes wide as he glanced up at the ceiling and relaxed his posture. “Like, me and Lisa weren’t a good match, but I miss the whole…  _thing_ , sometimes, y’know?”

Blinking at his friend, Castiel’s voice was laden with impatience when he said, “No, I don’t.”

"It’s pretty great, Cas.”

Focusing intently on the floor beneath his chair, Castiel shook his head. “Prove it,” he mumbled.

Dean looked thoughtful for a moment before his face lit up, a smirk forming on his lips as he sprang up from the bed. “Okay,” he said. “I will.”

Squinting at his friend, Castiel asked, “How?”

“I’ll take you out tomorrow night.”

His lips parting ever so slightly, Castiel blinked at the boy across from him and tilted his head. “What?”

“I’ll show you how great dating can be,” Dean said, nodding as he grinned. “I mean, it’ll be like practice for when you finally go out with someone.”

It took Cas a few seconds to process what he heard, and he widened his eyes when he realized Dean had pretty much just asked him out. “Dean, I-“

“Ah, ah, ah! No!” Dean pointed at his friend, shaking his head as he grabbed his backpack and began backing away toward the door. “I’m picking you up tomorrow night at six. Don’t worry about dressing up. I mean, don’t just wear jeans and a t-shirt, but don’t wear a tux, either.”

Standing from his chair as fast as he could, Cas stumbled across the floor and followed Dean out of his room. “Wait, I… Where are we going?”

Dean shrugged, opening the front door with a smile. “I’ll figure it out before tomorrow. See you then,  _sweetheart_ ,” he said with a wink, leaving his friend to stand alone in shock.

 

Castiel’s heart was pounding in his chest. He glanced at the kitchen clock from where he sat at the table.  _5:57_. Dean was due out front in three minutes. Standing from his chair, Castiel began to pace the floor. He stopped in front of the mirror on the living room wall and thinned his lips at his wide-eyed reflection. Why was he nervous? It wasn’t even a real date. What was there to worry about?

“What’re you all dressed up for, little bro?”

Squeezing his eyes shut, Castiel turned around and clenched his fists. “Not now, Gabriel.” He opened his eyes and glanced down at his white button-down shirt, frowning as he asked, “Do you really think it looks like I’m dressing up?”

“Depends… where are you going?”

“I don’t know,” Cas sighed. “But I’m leaving in less than three minutes and I don’t have time to change so if this is too fancy for wherever it is that I’m go-”

“Dude, calm down,” Gabriel interrupted, waving a hand. “You look fine. The jeans dress it down, don’t worry about it.”

“But do they dress it down too much?”

Gabriel let out a sound that was something between laughter and a huff, turning his head away from his younger brother. “Really, Castiel? Are you going on a date or something?”

Like a deer in headlights, Cas blinked at his brother. “I… Um…”

The Impala’s horn broke the silence, causing Castiel to nearly jump out of his skin.

“Who is that?” Gabriel asked with raised brows, moving to the window and beginning to peel back the curtain before his brother rushed over and stopped him with a pleading look. “Ah, come on, Castiel-”

“I’ll be back… um… later.”

 

“I would’ve done the whole knocking at the door thing,” Dean began when his friend entered the car, “but, uh, I didn’t know if your family was home or if that’d be too weird.”

Castiel avoided eye contact with the boy as he shook his head and buckled his seatbelt. “Gabriel’s there, and probably straining to see us from the window right now,” he said with a frown, “but I don’t think he can see too well in this light.”

“Right,” Dean said, then let out a deep breath as he put the car into drive and pulled out onto the street. “Nervous?” he asked, a small smirk forming at the corner of his mouth as he glanced at Castiel.

“Yes,” the boy admitted. “Are you?”

Dean’s bottom lip protruded as he shook his head. “Nope.” He nudged his friend with his elbow and smirked. “Good to know I gotcha all flustered, though.”

Rolling his eyes, Castiel turned to look out the window. “Shut up, Dean.”

 

It was quiet in Red Robin, for a Saturday night. Still, it was crowded enough that the boys had to sit at a table rather than a booth. Dean made sure they were seated in a corner, out of view, just in case anyone they knew decided to dine out that night.

“Sorry,” the freckled teen said as soon as the host left them, “I know this isn’t, like, the most fancy place. It’s the best I could afford, y’know?”

Castiel’s brows drew together as he blinked at his friend. “You’re paying?”

Dean smirked, leaning back in his seat. “Of course I am! That’s the responsibility that comes with asking someone out. Geez, Cas. I’ve got a lot to teach you, don’t I?”

Reaching for his menu, Castiel averted his gaze to the table and sighed, “So it would seem.”

Thinning his lips, Dean eyed his friend before leaning forward, folding his arms on the table. “Hey, don’t feel bad about it,” he said, his voice low but firm. “I’m not trying to pick on you or anything, I swear.”

“Fine,” Cas snapped, letting the menu fall from his hands as he met Dean’s gaze. “Tell me what one typically does on a date, then. What are we going to talk about?”

Sighing through his nose before straightening his posture and forcing a smile, Dean said, “Ourselves. Tell me about yourself, Cas.” He gestured at his friend with an open hand.

“You already know about me, Dean. We’ve been friends for-”

“We’re not friends,” Dean interrupted. “This is a date, remember?”

Castiel’s frown twisted into one of confusion as he stated simply, “I don’t understand.”

“This is practice, for when you’re on a  _real_  date. You have to learn how to flirt, Cas. Christ, just… compliment me on something.”

Glancing around him, Castiel shifted in his seat and sighed. He ran his gaze over Dean’s face and torso for a moment before saying, “You have lovely eyes, Dean.” Cocking his head to one side, Cas added, “I like your freckles, too.”

Dean swallowed, his mouth parting as he scanned his friend’s face before taking a deep breath and nodding. “Right,” he said, straightening his posture, “see, that’s good. Now ask me something about myself.”

Quirking a brow, Cas couldn’t hide his smile as he asked, “Will my other, ‘ _real_ ’ dates be this demanding?”

Dean chuckled, leaning back in his seat and running a hand through his hair. “Sorry, man. Let’s just, uh…,” he paused to make eye contact with his friend and smiled. “Let’s just talk like we usually would, then. That’s how normal dates are supposed to go, anyway.”

"What do you mean?”

“I mean,” Dean began, glancing at the server approaching their table as he sat up, “just be yourself.” He nodded at his friend. “Know what you want?”

“No.”

“Well, how about we just split something? It’s a dumb little cute thing couples do sometimes.”

 

As they were just about finished with the deluxe burger Dean ordered for them, their server stopped by to ask about dessert.

“I dunno, what do you got?” Dean asked the blonde teen, giving her a sweet smile. The orange light made him seem so inviting, so warm. Castiel bit his tongue and looked away.

The girl grinned back at the hazel-eyed boy and said, “We’ve got the Mountain High Mudd Pie. It’s pretty amazing.”

“Sounds sweet,” Dean said with a smirk. The girl giggled and asked if he’d like any. Dean nodded, then blinked and gestured at the boy across from him. “Oh, we’re gonna split it, though.”

“I’ll bring two plates,” the server nodded. “Anything else for you?”

Shaking his head, Dean beamed at the girl and said, “Nope, you got me taken care of pretty good.”

Castiel clenched his fist, digging his nails into his palm in effort to distract himself from the urge to kick his fake date in the shin. When the girl walked away with a grin, Cas glared at Dean.

The smile fell from the teen’s face when he met his friend’s accusing gaze. “What?”

Rolling his eyes, Cas shifted in his seat and folded his arms over his chest, staring intently at a framed poster of Marilyn Monroe on the wall.

“Oh, come on, Cas, I was just… It’s not like we’re  _actually_  going out, anyway.”

Castiel bit his tongue, cursing himself for feeling… whatever the hell he was feeling. Dean was right, they weren’t a real couple. Why did it upset him so much? “This was your idea,” he mumbled, slowly bringing his gaze to Dean’s. “You’re supposed to be showing me how to behave on a date. I may be inexperienced, but I’m fairly certain that flirting with the waitress is not proper date etiquette.”

Raising his hands in defeat, Dean nodded. “Okay, you got me, I messed up. Sorry.” He bit his lip before adding, “Hey, I’ll make it up to you, okay? We’ll do this again. We’ll do something else.”

Snapping his head up, Castiel frowned at his friend. “What?”

"I dunno,” Dean shrugged. “We’ll go bowling or something.” Smirking as he saw the girl bringing their dessert to them, he added, “First, you gotta let me feed you some of that pie.”

“Feed me?” Castiel asked, his eyes widening at the thought of his friend bringing a forkful of food to his lips.

Dean winked at the other boy as the server set the plate down in front of them, and Castiel looked away as his cheeks turned pink. Dean couldn’t help but chuckle as he picked up his fork.

“Oh, I forgot the other plate and silverware!” The server gave Dean an apologetic smile and said, “Let me take care of that for y-”

“Don’t worry about it,” Dean interrupted, waving a hand as he smiled. He made sure Castiel was meeting his gaze before he said, “I’ll just feed him. He’s my  _date_ , after all.”

Looking from one boy to the other, the girl widened her eyes and backed away with a smile. “Oh. Okay, then. Have a nice evening, you two. I’ll bring your receipt in a few minutes.”

"Okay,” Dean said, not bothering to break eye contact with Castiel as he gathered a bite of pie onto his fork and lifted it to the other boy’s mouth. He wiggled his eyebrows, smirking as he let the dessert smear across his friend’s bottom lip.

Castiel’s heart leaped in his chest as he finally opened his mouth, and Dean slipped the fork inside. Dean Winchester, his best friend since middle school, was feeding him pie. On a date. At that point, Cas didn’t care if it was fake. It felt real. It seemed as though Dean was deliberately trying to  _make it_  real. Could it be?

“Good?” Dean asked, one brow cocked as he brought the fork back to the plate and smiled at his friend.

It took Cas a few seconds, blinking at the other boy, before he could manage to croak, “Yes.”

“Good,” the boy beamed, getting a forkful for himself and eagerly taking a bite. His brows shot up as he nodded at his friend. “Yeah, I’m gonna have to agree with you, Cas. This is amazing.”

“Y-yes.”

Dean gave Castiel a knowing smirk and leaned forward in his seat. “Want some more?” he asked, his voice like honey.

“Yes.”

 

The next outing the pair made as a “fake couple” was to a miniature golf course. Dean decided against bowling on the grounds that it was “too crowded to talk there”. So, Cas found himself standing on fake grass, in jeans, a t-shirt, and Dean’s jacket. He’d merely mentioned the breeze when they stepped out of the car and Dean had shrugged his outerwear off and draped it around his friend’s shoulders. “It’s a dating thing,” he’d explained.

“Hey, just so you know,” Dean said as he bent over to grab his golfball out of the third hole, “that whole dessert thing was… a bit much, for a first date. Normally, that wouldn’t happen.”

Following his friend to the next hole, Castiel asked, “Then why did you do it?”

Dean shrugged, a bashful laugh escaping his lips as he set his ball on the tee mat and lined up his putter. “I dunno. Seemed like a good idea at the time.”

“Well, it was… strange.”

Taking a short swing, Dean watched the ball roll over the little hills and smiled, then turned to his friend. “Good strange or bad strange?” he asked.

“I’m… not sure.”

“You’re up,” Dean said quickly, turning away and pointing at the mat.

A small smile crossed Castiel’s face as he shook his head. “Technically, I was supposed to go first,” he said, “but, okay.”

“C’mon, man, I’ve only played this, like, two times,” Dean said, chuckling as he leaned against the fence. “Give me a break.”

“I’ve never done this before,” Castiel stated.

“Mini-golf?”

“Yes.” Castiel sighed, dropping his gaze to the putter in his hands. “I’m not even sure I’m holding this right.”

“You’re kidding,” Dean said, his voice flat as he swept his gaze over his friend’s rather pathetic stance. “You’re doing that on purpose.”

“I assure you, I am not.”

Dean smirked and moved to Castiel’s side. “Well, then,” he said, positioning himself behind his friend and bringing his arms around so he could hold Castiel’s, “I’ll just have to show you what you’re doing wrong.”

“I thought you didn’t know wh-”

“Holding a stupid golf stick thing is not rocket science, Cas,” the boy interrupted, gripping his friend’s hands in his own and making them pull the putter back. “Just pull back… and…,” Dean paused as he brought their arms forward, “swing!”

The boys watched as the ball successfully made its way into the hole. Dean backed away from his friend and gave him a smug grin. Castiel merely shook his head and smiled to himself before they continued to the next hole.

 

“Should I, uh… I should probably walk you to your door, this time,” Dean said as he pulled up to Castiel’s house later that evening. He unbuckled his seatbelt and put the car into park, looking to his friend with raised brows.

Castiel was lost in the other boy’s eyes for a moment before he blinked and nodded. “Right, okay.” He unbuckled his seatbelt and moved to open the door.

“Wait! I’ll get that,” Dean said, jumping out of the car and running to the passenger side. He opened the door with a smile on his face and nodded at Castiel. “Sir,” he said, grinning dumbly as he extended his arm, “I sure enjoyed our time tonight.”

Barely holding back his laughter, Castiel took Dean’s arm and nodded as he exited the vehicle. “I enjoyed it, as well.”

The pair walked, arm in arm, to the front door. Dean was beaming, and Castiel couldn’t tell if it was because he thought it was funny, or if he was genuinely happy. Cas couldn’t really tell what he,  _himself_ , was feeling.

When they stopped, Dean dropped his arms to his sides. He began to shift back and forth on his feet, bringing a hand up to play with the short brown hair at the back of his neck as he stared intently at the ground. “So… usually, when dates end… um, sometimes… people will, uh…,” Dean took a deep breath and met the other boy’s gaze. “People usually kiss right about now.”

Castiel gulped. “Oh.” His heart pounded in his chest, and something strange was happening in the pit of his stomach. After a few seconds passed, he could no longer hold Dean’s gaze. “I, um… Are we going to do that?”

“I-I dunno. D’you want to?”

“I don’t know.” It was a lie, and Castiel recognized it the moment it left his lips. He definitely  _wanted_  to, he just didn’t want to freak Dean out. He swallowed hard, forcing himself to look his friend in the eye as he said, “Maybe we should. It’s part of the dating experience.”

Nodding quickly to himself, Dean agreed, “Yeah, it’s super important for all that.”

“Right.”

“Okay.”

Cas closed his eyes as Dean leaned forward, slowly, and he sucked in a quick, small breath when he felt the warmth of his friend’s mouth on his own. It was only a sweet, two second kiss before Dean was pulling away, but it left Castiel breathless, nonetheless.

“Uh, right,” Dean said, bringing a hand up to rub nervously at the back of his neck. “Goodnight, then.”

“Goodnight, Dean,” Castiel managed to say, his vision going out of focus as he stared blankly ahead. He hardly noticed Dean returning to his car, only reaching for his keys when the Impala’s headlights turned on, causing him to squint.

As soon as he was inside, Gabriel greeted him with a grin. “Have a good night, little bro?”

 

“You forgot your jacket last night.” Castiel dropped the piece of clothing in front of Dean during lunch at school the next day, earning an amused stare from the boy’s brother, who sat across from them.

“So  _that’s_  where you were!” Sam said with a grin. “Dude, you told me you were going on a date with someone. What-“

"Shut up, Sammy.” Dean snatched up his jacket and crammed it into his backpack without a word. He avoided eye contact with Castiel at all costs as he finished his slice of pizza.

Pursing his lips, Castiel squinted at his friend after a few minutes of silence and shook his head with a sigh. “Do we need to talk, Dean? In private?”

“Nope.”

Cas clenched his jaw, standing from the table and laying a hand on Dean’s shoulder. “I think we do.”

“Nope, we’re good.”

“Dean,” Cas demanded, glaring at his friend when they finally made eye contact.

 

The boys’ bathroom wasn’t empty, but that didn’t stop Castiel from speaking his mind right then and there. “Do you regret kissing me?” he asked as soon as they were inside.

Dean glanced around and clenched his jaw. “I don’t know,” he mumbled after a wide-eyed student left the room. He glared at his friend when he heard the laughter in the hall.

“Forget about him, Dean.” Tilting his head, Cas asked, “Is that what the problem is? Are you worried about what people will think?”

Moving to lean against the sink, Dean shrugged. “I dunno.” 

“Dean. What is going on between us right now?”

“I. Don’t. Know.”

“Why did you kiss me if you didn’t want to?” Castiel demanded through gritted teeth, his eyes watering.

Sighing, Dean dragged a hand down his face. “I didn’t… I didn’t  _not_  want to.” Shifting against the sink, Dean frowned at his friend. “Don’t do that.”

“What?”

“Don’t…  _cry_  like that,” Dean said, wincing.

"I’m not crying yet, Dean. I’m… I’m angry.”

“Why?!” Dean’s voice loudened as he stood up straight and pointed at his friend. “ _You’re_  the one who said we should kiss. I asked you if you wanted to, and  _you_ agreed to it.”

"I’m not angry that it  _happened_ , Dean, I’m angry that you were avoiding me earlier! I’m angry that you seem to regret it!” Beginning to pace the tiled floor of the bathroom, Castiel shook his head. “I’m angry that you started this whole thing because you felt  _bad_  for me. I’m angry that you asked me out and then flirted with that girl. I’m angry that you didn’t even stop to consider that maybe _,_  just  _maybe_ , I might actually  _want_  to date you.”

Dean blinked at his friend, frozen where he stood. “You… you wanted to date me?”

Castiel gave the other boy a helpless frown, his bottom lip quivering as he sunk to the ground. He gathered his knees against his chest and buried his head as the tears began to fall from his eyes.

"Shit, Cas,” Dean whispered, moving to his side in seconds. He put an arm around the boy and said, “I didn’t know.”

“Clearly.”

“I wasn’t thinking,” the taller boy admitted. “When I asked you out, I wasn’t thinking. I didn’t know I’d realize how… how much…”

Lifting his head, Castiel frowned at his friend. “How much what?”

Dean bit his lip before meeting Castiel’s gaze. “How much I like you.” Shifting where he sat, the boy smiled. “And I do, Cas. I like you. And I think part of me already knew that, but… I never gave myself the opportunity to… to… Anyway, I… I dunno. When I asked you out, I had no idea it’d happen again. And I had no idea I’d kiss you. And I had no idea I’d  _like_  it. And-“

“Where is this going, Dean?”

“Where do you want it to go?”

“I love you,” Castiel stated simply.

Dean sat silently, blinking for a few seconds before finally saying, “Yeah. Me, too.”

“So,” the blue-eyed boy began, moving to his feet and taking Dean’s hand in his own, “what are we?”

Following Castiel’s lead, Dean stood and smiled. “We’re… ‘us’, I guess.”

“Well, then… would it be appropriate for ‘us’ to kiss?”

Dean glanced around the room before quirking a brow at the other boy. “In here? Right now? This isn’t the best atmosphere, Cas.”

“Okay,” Castiel nodded. “Well, if you’ll wait a few hours, I’d like to…,” the boy chuckled to himself, looking down and biting his lip before smiling back up at Dean. “I’d like to go out with you after school.”

The smirk on Dean’s face spread into a wide grin as he asked, “Are you asking me out on a  _date_ , Castiel?”

“Yes. And, I can assure you, I have been well trained in the ways of dating.”

“I dunno, I heard your teacher was a bit of an idiot.”

Cas frowned. “You’re not an idiot, Dean.”

“Yeah, I kind of am.” Stepping closer, Dean gave the other boy a bashful smile. “I should’ve asked you out, like, months ago.”

Averting his gaze to the floor, Castiel mumbled, “A couple years ago would’ve worked for me.”

“ _That_  long? Seriously?” Dean’s lips parted as he reached for Castiel’s hands. “Dude, you should’ve said something. Would’ve saved me from a few bad relationships.”

“Well, I didn’t know for  _sure_  how I felt about you until I was waiting to be picked up that first night.”

"You really were nervous, huh?” An endearing smile brightened Dean’s face as he leaned closer. “Y’know, kissing here doesn’t sound like  _that_  bad of an idea.”

Lifting a brow, Castiel smirked. “You don’t want to wait until we’re back at my place?”

Dean practically whined when Castiel backed away. Then, he followed him into to the hall. “Is that where we’re going for our date? Your house?”

"Yes. I’m going to bake something for you.”

Licking his lips, Dean slid his arm around Castiel’s waist as they walked back into the cafeteria. He ignored the stares they got from the other students as he asked, “What’re you gonna make me?”

“Pie, probably.”

“Sounds awesome. Will anyone be home?”

“Gabriel might, but he already knows.”

Dean stopped in front of their table. “You told him?”

Shaking his head, Castiel explained, “He was behind the door last night. He heard the car pull up to the house and kinda spied on us.”

“Nosy bastard,” Dean mumbled as he took a seat.

“Who’s nosy?” Sam asked. “And where’d you two go?”

“ _You’re_  nosy,” Dean said, smirking at his brother. “And we went to the bathroom. To talk about our relationship. Because, yes, that’s a thing, now. And if you laugh, or tell Dad, I’ll hire a clown to stand outside your bedroom window every night for the rest of your life.”

Sam’s eyes widened as he raised his hands. “Dude, I’m not laughing.” He focused his attention on his lunch, then mumbled, “I knew it, though.”

“Congratulations,” Dean said. He turned to smile at Castiel. “Y’know what?”

“What?” Castiel asked, a curious smile forming on his lips.

“I’m gonna kiss you.”

“You should wait until you’ve tried my pie,” Castiel said with a grin. “You’ll probably be a bit more enthusiastic about it, then.”

Beaming, Dean nodded. “It’s a date.”


End file.
